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Living With Ross Ulbricht: Housemates Say They Saw No Clues Of Silk Road Or The Dread Pirate Roberts

A photo from Facebook shows Ross Ulbricht and his sister in Sydney in Dec. 2011. According to the FBI, the Silk Road, an online narcotics marketplace, started operating in 2011. (Photo via Facebook)

To the hundreds of thousands of online users of the Silk Road narcotics marketplace, he may have been known by the swashbuckling alias, the Dread Pirate Roberts. To the FBI, he was known as Ross Ulbricht, a 29-year-old former physics student turned criminal mastermind.

To his housemates, he was simply “Josh,” a quiet guy who joined them through Craigslist, kept to himself and spent full days buried in his laptop.

That all ended last Thursday morning, when 30-year-old San Francisco resident Brandon picked up a copy of the San Francisco Examiner on his way to work. There, on the front page, was his former housemate’s face under the headline “Online Drug Market Closed.” Snapping a photo, he texted it to another housemate Drew along with a message: “Funny. Looks kinda like our subletter.”

He received a quick response. “Not looks like. Is.”

For seven weeks this summer, Brandon had been living with a man who identified himself to be Joshua Terrey, a subletter who claimed to be a freelance currency trader that had just come back from Australia. Last Tuesday, the FBI arrested “Josh,” identifying him as Ross Ulbricht and charging him with money laundering, narcotics trafficking conspiracy and computer hacking as the alleged head of an internet drug bazaar that generated about $1.2 billion in revenue since early 2011. According to the FBI, Josh, Ulbricht and the Dread Pirate Roberts—the online name of the leader of Silk Road—were the same person.

“He seemed like a normal guy,” says Brandon. “Obviously he had a dark side, but he never showed any of that.”

In the nearly two months he lived with Brandon and a third unnamed housemate in San Francisco’s family-oriented West Portal neighborhood, Ulbricht was “friendly” and “polite.” Unlike the criminal complaint, which portrayed an online life of alleged hit jobs and drug dealing that read like a Vince Gilligan television script, the stories provided by the individuals who lived with Ulbricht paint a rather vanilla picture of daily monotony.

Both Brandon and Drew–who subletted Ulbricht his room while he and his wife traveled for work–asked that their last names be withheld because of privacy concerns, but did allow FORBES to meet with them at their current home where they have been living for more than seven years. They also asked that their address remain anonymous and that any distinguishing features of their home remain unpublished.

From their living room, the pair recounted their interactions with a man who was pursued by the FBI, and who, according to criminal complaints, amassed more than $80 million in commissions from operating an illicit website. Yet, however wealthy he supposedly was, Ulbricht shared a temporary home and had few possessions, hiding in a residential San Francisco community far away from the bustle and bright lights of downtown. He kept to himself, says Brandon. Despite the occasional walks around the neighborhood or trips to the local Safeway, he mainly stayed in his room, hunched over his black laptop and doing things beyond the scope of his housemates’ understanding.

Ulbricht first connected with his future housemates via Craigslist in late June 2013, responding to an online ad for a “Furnished Summer Sublet” at 15th Avenue that was available for $1,200 a month. A criminal complaint filed in the Southern District of New York originally identified the home at 15th Street, however an FBI spokesperson confirmed to FORBES that that was “a typo.” In an anonymized email (Craigslist often anonymizes its users’ emails to prevent fraud), Ulbricht said he had recently moved to the area and needed to find a place soon, identifying himself as a “29 yo [sic] Texan man, good natured and clean/tidy.”

“I am a currency trader and do some freelance IT work as well,” he wrote. “I mostly keep to myself, spending most of my time working, but enjoy going out and socializing from time to time.”

Text messages sent between Ross Ulbricht’s housemates Drew and Brandon. Both housemates only knew Ulbricht as “Josh.” (Photo: Ryan Mac)

In corresponding with Drew’s wife, he revealed more details. He didn’t have a cell phone, said he was temporarily staying in a hotel in Redwood City, Calif.–a Bay Area suburb 45 minutes away–and wanted to pay all in cash. Drew, a 31-year-old professional musician who was leaving with his wife to play at an opera festival at the time, noted that he wasn’t suspicious at the time.

“He told us he had just come from Sydney and had been in Australia, which is whatever,” he recalled. “It’s like: ‘Ok you’re back from abroad, so you don’t have a cellphone yet and you’re staying at a hotel in Redwood City. That’s near the airport. O.K.’”

Ulbricht, according to the criminal complaint, had been living in San Francisco prior to contacting the house on 15th Avenue. A video on YouTube that has since been removed showed him discussing his move to the city around fall 2012 to stay with a friend René Pinnell, who has denied any knowledge of Ulbricht’s alleged association with Silk Road. Ulbricht reportedly moved out of his friend’s home because Pinnell had moved in with a fiancée.

Information found on Facebook does seem to verify that Ulbricht was in Australia sometime around late 2011. Multiple images posted of him by his sister Cally Ulbricht on the social network show the pair being photographed Down Under, with one photograph hinting that the two were around Sydney for the holidays. One paper in Australia reported that Ulbricht lived in a house on Sydney’s Bondi Beach for six months.

In screening “Josh,” though, Drew says he had little time to focus on what seemed like small talk at the time. He was leaving in a matter of days and wanted to make sure that he found an occupant that could cover the rent while he and his wife were gone. After a short tour where he met the roommates, Ulbricht paid $2,026 dollars up front in cash and moved into the master bedroom of the three-bedroom home on June 21, 2013. He had next to nothing–just a computer and three or four changes of clothing, says Brandon.

Ulbricht’s stay at the house was utterly, even studiously, unremarkable, say his housemates. Rarely showing emotion, the man they knew as “Josh” shared little about his life, once noting that he had friends in Texas but had since cut off ties. Never once did he mention his family, which, based on FORBES’ conversations with relatives, he was fairly close to.

Strictly implying he did currency trading, Ulbricht worked from his laptop for about eight hours a day and claimed he did “four transactions a week” says Brandon. There was no talk of Silk Road or the anonymous currency, Bitcoin. A third housemate curious as to what Josh was doing on his computer once noticed the laptop was left open and wandered into Josh’s room to take a look. After watching lines of green text scrolling and updating across a screen without being able to decipher what exactly was going on, he walked away.

“We were perfect for him,” says Brandon. “We didn’t ask a lot of questions. I mean it was like: ‘How’s it going?’”

Occasionally watching Netflix with Brandon or sharing a beer in the living room, Ulbricht was more often seen curled up in a living roof sofa reading—possibly sci-fi novels from the local library–when not at his computer. There were never conflicts with “Josh,” whose only memorable oddity, according to his housemates, is that he often walked around without a shirt. One neighbor, a former policeman, later recalled seeing Ulbricht topless one day to Drew, noting that he made small talk with him about the sunshine: “Don’t get used to that weather!”

Barring the occasional polite conversation, Ulbricht, was a loner in his time at the 15th Avenue house . He cooked steak dinners for one and never had anyone over. He rarely ventured out at night. He spent July 4 at home, recalls Brandon.

The Dread Pirate Roberts spent the Fourth corresponding with FORBES. Refusing to do an interview in person or reveal any personal details including a real name, the Silk Road head was on the other side of an anonymous chatroom for the better part of five hours, answering questions about the website’s past, present and future. That conversation would later form the bulk of the first published magazine interview with the criminal mastermind, in which he revealed personal details like “smoking a bowl of sticky indica buds at the end of a long day.”

Josh was never seen with any type of drug, says Brandon. Ulbricht’s room, which was kept clean with the bed made every day, showed no signs of narcotics use, according to the housemates. Moreover, there were never any packages coming and going from the home.

One package that had been deceitfully addressed to Drew but intended for Ulbricht, however, never made it. In the criminal complaint, an FBI agent notes that U.S. Customs seized a package at the Canadian border around July 10 that contained “nine counterfeit identity documents.” All the documents had the same photograph of Ulbricht.

Ulbricht was visited two weeks later at the 15th Avenue home where he was questioned by a Homeland Security Investigations (HSI) agent about the documents. “Ulbricht volunteered that ‘hypothetically’ anyone could go onto a website named ‘Silk Road’ on ‘Tor’ and purchase any drugs or fake identity documents the person wanted,” reads the complaint. It’s unclear how customs actually homed in on finding those counterfeit documents or whether the Department of Homeland Security (DHS) was aware of the FBI’s concurrent investigation. The public affairs office for the DHS, did not respond to requests for comment. A spokesperson for the FBI told FORBES only that “this was a multi-agency investigation to include FBI, DEA and HSI.”

To Drew, who was eventually contacted by the HSI agent, it didn’t initially seem like the agency was interested in Ulbricht for any activity related to Silk Road. The agent seemed more interested in the quantity of fake IDs, he says, as well as tracking down the counterfeit ID provider. To date, Drew says the FBI has yet to contact him or his housemates.

Ulbricht wasn’t immediately bothered by the agent’s visit either. Coming up toward the end of his sublet, he continued to stay at the house more than a week after the initial visit from the HSI agent. Brandon notes that he was often leaving the home around this time to supposedly search for another sublet, and at one point, borrowed his phone to make a call to a friend whom he said was getting married. That phone number, which was left in Brandon’s call history, belonged to Pinnell.

Pinnell did not return requests for comment.

For unknown reasons and without notice, Ulbricht left the home more than a week before his sublet was officially over. According to Brandon, who had left the city during the first weekend of August, Josh had left by Aug. 2, returning two days before the end of his rental term on Aug. 11 to return the keys. He entered the house without being seen, left the keys on the dresser of his room and left.

The next time the housemates saw Josh, his photo was on the front page of the Examiner.

On Wednesday, Ulbricht, through a public defender, denied all charges in a San Francisco federal court but did verify his real identity. Unshackled and wearing a red Alameda County prison jumpsuit, he constantly looked over the crowd for the few minutes he was in the courtroom before his representative agreed for him to be transferred to New York. Ulbricht can make a request for bail from New York.

For Drew, it’s unclear why a man with the supposed amount of money he had never left the country.

“I don’t entirely understand what his motivation was,” he says. “[He was] talking a little bit about maybe starting a family in the next few years and getting to know San Francisco and live life more and he’s got all this money and he just sits in a not-particularly nice rental house in the Sunset [District] and just f***s around on the computer all day until he gets sent to prison.”

Brandon, who says he initially felt a little weird about sharing his home with Ulbricht, doesn’t seem to have lost any sleep.

“We’re probably an afterthought to him now,” he says. “We’re just the place of where he was for a couple of months. We never pissed him off or anything—that I know of. Drank all his milk or something. I don’t know.”

The pair of housemates, both avid Breaking Bad fans, likened their situation to the main character’s son, who remained unaware of his father’s narcotics involvement on the show.

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His motivation to stay in the US was to conduct his experiment and illustrate the potentials of his ideology (developed from the Mises Institute and Austrian market ideals), and it is extremely important not to ignore this premise. His ideology wasn’t the legalization of drugs (and definitely not to encourage hits or weapon sales, as many articles suggest), but rather an attempt to return the US to a truly free-market system. This seems like a stretched belief to some, but if you logically think about it, a drug market was a perfect forum to conduct his experiment (bitcoin, tor, no taxes or regulations that hinder profit or operations, and the huge demand for controlled and regulated drugs, but no open suppliers). The drug trade made his point easy to capitalize on.

I have no doubt that Ross was a normal person who loved his country (but not the direction of government’s growing influence in the economy) and just wanted to see his ideals actually play out, but it meant evading laws that we have become accustomed to. In our current society, when a law is broken, we gasp and belittle the instigator as if the law always represents a puzzle piece to ethical truth. If the government best advises ethical truth, why is it that the CIA and similar operations can make drone strike mistakes without accountability, but whistleblowers like Snowden are sentenced time in jail for clearly trying to introduce transparency, not aide the enemy with intel. The motives and conviction do not match the underlying ideology in either case.

Many believe that government presence in the economy is generally bad for the health of the economy. However, it does benefit a small group of powerful people. This is the base belief for the Mises Institute and Ross’ ideology. This has been proven in documentation and in a video that has recently shocked people who follow their intuitions about wealth distribution. The video can be found by searching “Wealth Inequality in America.”

Is that really what was happening? I mean you have knowledge that is what Ulbricht was doing? If it is the reason for what he did in creating the Silk Road site, I am even more impressed with him. Not only does he have business sense and the ability to identify a viable market(even though it is declared illegal by a bunch of bureaucrats who gain from those laws) he succeeded up and over and beyond anything he may have thought possible when forming his plan. A plan of pure liberty and freedom based principals he hoped would allow him to conduct his experiment, proving that gov’t involvement in every aspect of our lives is not needed or even proper. That commerce was not created in order to give gov’t a source of revenue, it was created to provide a service or product in exchange for some form of compensation outside the regulatory thugs who regularly over reach authority throughout govt.

Very well written Nick. I couldn’t agree more. To me he’s a legend, someone aiming at bringing true liberty. The government has no place in peoples private affairs. Like Snowden, Manning, Assange… this many is not a criminal. Those who are trying control human destiny are the criminals and should be locked up. The US is fast becoming a fascist police state. Many people are not happy with this. This man is a hero.

Incredible statement Nick. And, to the extent of my knowledge, it’s all completely true. This is not an issue of drugs, nor is it an issue of untaxed income. This is an issue about ideals, ethics, and rationality. Dread’s mission was to shed light on a corrupt system and create an environment where a free market could truly exist. Well done in pointing that out, Nick.

Despite the tinge of sarcasm, I do agree with your sentiments. It’s easy to target A individual (i.e. Ross) by a nebulous organization/adversary (i.e. FBI) with unlimited resources — especially when he [Ross] is a potential threat to their own pliant nature of justice and modus operandi.

Thanks for the comment Richard. I wrote a little about that video in an earlier post as well: http://www.forbes.com/sites/ryanmac/2013/10/02/who-is-ross-ulbricht-piecing-together-the-life-of-the-alleged-libertarian-mastermind-behind-silk-road/